Thermally stabilized polyvinyl chloride compositions

Details Thermally stabilized polyvinyl chloride compositions Thermally stabilized polyvinyl chloride compositions

2001-07-17

2004-09-14

Mulcahy, Peter D. (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C525S204000

Reexamination Certificate

active

06790885

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to polyvinyl chloride compositions. The present invention particularly relates to flexible polyvinyl chloride compositions exhibiting high thermal stability.
2. Description of the Prior Art
Chlorine containing polymers in general and polyvinyl chloride (PVC) compositions in specific are well known materials having a wide variety of commercial uses. As are most polymers, chlorine containing polymers can be subject to thermal and oxidative decomposition. U.S. Pat. No. 6,096,820 to Lockledge, et al., describes using a synthetic crystalline aluminosilicate to impart thermal stability to PVC. Materials such as the aluminosilicates can impart properties to polymers which are not always desirable.
Other materials are known in the art to act as stabilizers. For example, the patents DE 1694873, U.S. Pat. Nos. 4,656,209, 5,925,696, GB (A) 2,318,188A, EP (A1) 967 209, EP (A1) 967 245, and EP (A1) 967208 describe using monomeric aminouracyls and aminothiouracyls as PVC stabilizers.
It would be desirable in the art of preparing chlorine containing polymers to prepare such polymers with stabilizers which allow for the preparation of a fully transparent stabilized system which can be processed at high temperatures for long periods without staining or blistering. It would also be desirable in the art to prepare such polymers where the polymer is PVC. It would be even more desirable in the art if the PVC were a flexible PVC.
SUMMARY OF THE INVENTION
In one aspect, the present invention is a chlorine-containing polymer composition exhibiting high thermal and oxidative stability comprising a chlorine-containing polymer and a stabilizer selected from the group consisting of oligomeric aminouracyls, polymeric aminouracyls and mixtures thereof.
In another aspect, the present invention is a stabilizer composition suitable for the stabilization of chlorine containing polymers comprising an oligomeric and/or polymeric aminouracyl compound having a structure of: (a) repeating units of general formula (I):
wherein:
R is selected from the group consisting of H; a C
1
-C
18
linear or branched alkyl; a C
5
-C
8
cycloalkyl; an aryl; an aryl substituted with —OH or C
1
-C
8
alkoxy (here and hereafter called “substituted aryl”); an arylalkyl; an alkylaryl; and mixtures thereof;
R
1
is selected from the group consisting of H; a —(C═O)—C
1
-C
12
linear or branched alkyl; a —(C═O)—O—C
1
-C
12
linear or branched alkyl; a —(C═O) phenyl, wherein the phenyl is unsubstituted or substituted with —OH; a C
1
-C
8
linear or branched alkyl; a C
1
-C
8
alkoxy;
and mixtures thereof; and
Z is O or S;
(b) linking groups between the repetitive groups of formula (I) which are the same or different and are selected from the group consisting of: (CR
2
R
3
)
n
—, wherein n is an integer having a value of from 2 to 12 and R
2
and R
3
can be the same or different and each independently of the other is selected from the group consisting of H, a C
1
-C
12
linear, branched or cyclic alkyl, and mixtures thereof; 3-methylene-3,5,5-trimethylcyclohexan-1-yl; methylenebis(4-cyclohexyl); methylenebis(3-cyclohexyl); 1,4-phenylene; 1-methyl-2,4-phenylene; 4,4′-diphenylenemethane; and mixtures thereof;
(c) terminal groups selected from the group consisting of: H; a C
1
-C
18
linear or branched alkyl; a C
5
-C
8
cycloalkyl; a C
3
-C
18
alkenyl; an aryl; a substituted aryl; an arylalkyl; an alkylaryl; a C
1
-C
18
hydroxyalkyl; a C
2
-C
18
alkoxy alkyl; a C
6
-C
10
cycloalkoxyalkyl; a C
7
-C
14
alkoxyaryl; a C
7
-C
14
aryloxyalkyl; a C
2
-C
8
alkylthioalkyl; a C
6
-C
10
cycloalkylthioalkyl; a C
7
-C
14
arylthioalkyl; a C
7
-C
14
arylthioalkyl; a C
1
-C
18
alkylamine, disubstituted with a C
1
-C
18
linear or branched alkyl; and mixtures thereof.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
According to the present invention, flexible PVC compositions with high thermal stability can be prepared using oligomeric and/or polymeric aminouracyls as stabilizers. These stabilizers are compounds having a structure of: (a) repeating units of general formula (I):
wherein:
R is selected from the group consisting of H; a C
1
-C
18
linear or branched alkyl; a C
5
-C
8
cycloalkyl; an aryl; a substituted aryl; an arylalkyl; an alkylaryl; and mixtures thereof,
R
1
is selected from the group consisting of H; a —(C═O)—C
1
-C
12
linear or branched alkyl;
a —(C═O)—O—C
1
-C
12
linear or branched alkyl; a —(C═O) phenyl, wherein the phenyl is unsubstituted or substituted with —OH; a C
1
-C
8
linear or branched alkyl; a C
1
-C
8
alkoxy;
and mixtures thereof; and
Z is O or S;
(b) linking groups between the repetitive groups of formula (I) which are the same or different and are selected from the group consisting of: —(CR
2
R
3
)
n
—, wherein n is an integer having a value of from 2 to 12 and R
2
and R
3
can be the same or different and each independently of the other is selected from the group consisting of H, a C
1
-C
12
linear, branched or cyclic alkyl; and mixtures thereof; 3-methylene-3,5,5-trimethylcyclohexan-1-yl; methylenebis(4-cyclohexyl); methylenebis(3-cyclohexyl); 1,4-phenylene; 1-methyl-2,4-phenylene; and 4,4′-diphenylenemethane;
(c) terminal groups selected from the group consisting of: H; a C
1
-C
18
linear or branched alkyl; a C
5
-C
8
cycloalkyl; a C
3
-C
18
alkenyl; an aryl; a substituted aryl; an arylalkyl; an alkylaryl; a C
1
-C
18
hydroxyalkyl; a C
2
-C
18
alkoxy alkyl; a C
6
-C
10
cycloalkoxyalkyl; a C
7
-C
14
alkoxyaryl; a C
7
-C
14
aryloxyalkyl; a C
2
-C
8
alkylthioalkyl; a C
6
-C
10
cycloalkylthioalkyl; a C
7
-C
14
alkylthioaryl; a C
7
-C
14
arylthioalkyl; a C
1
-C
18
alkylamine, disubstituted with a C
1
-C
18
linear or branched alkyl; and mixtures thereof.
Preferably, in general formula I, R is selected from the group consisting of: H, a C
1
-C
18
linear or branched alkyl, a C
5
-C
8
cycloalkyl, an aryl, an aryl substituted with —OH or C
1
-C
8
alkoxy, and mixtures thereof; R
1
is H; and the terminal groups are selected from the group consisting of: H; a C
1
-C
18
linear or branched alkyl; a C
5
-C
8
cycloalkyl; a C
3
-C
18
alkenyl; an aryl; an aryl substituted with —OH or C
1
-C
8
alkoxy; a C
1
-C
18
alkylamine, disubstituted with C
1
-C
18
linear or branched alkyl; and mixtures thereof.
Oligomeric and/or polymeric aminouracyls according to the present invention have a mean molecular weight of from 280 and 5,000.
Oligomeric and/or polymeric aminouracyls according to the present invention are normally obtained by cyclization of an oligomeric and/or polymeric urea using cyanacetic acid or its derivatives. The product thus obtained can be further derivatized to give compounds where R and R
1
are different from H.
Preferably, the cyclization is carried out on a polyurea prepared by oligomerization and/or polymerization using suitable combinations of:
(A) a diisocyanate (DD) of formula OCN—Y—NCO wherein Y is selected from the group consisting of: —(CR
2
R
3
)
n
—, wherein n is an integer having a value of from 2 to 12 and R
2
and R
3
are the same or different and each independently of the other is selected from the group consisting of H, a C
1
-C
12
linear or branched or cyclic, and mixtures thereof; 3-methylene-3,5,5-trimethylcyclohexan-1-yl; methylenebis(4-cyclohexyl); methylenebis(3-cyclohexyl); 1,4-phenylene; 1-methyl-2,4-phenylene; 4,4′-diphenylenemethane; and mixtures thereof;
(B) an amine (A) of the general formula X—NH
2
wherein X is selected from the group consisting of: H; a C
1
-C
18
linear or branched alkyl; a C
5
-C
8
cycloalkyl; C
3
-C
~
alkenyl; an aryl; a substituted aryl; an arylalkyl; an alkylaryl; a C
1
-C
18
hydroxyalkyl; a C
2
-C
18
alkoxy alkyl; a C
6
-C
10
cycloalkoxyalkyl; a C
7
-C
14
alkoxyaryl; a C
7
-C
14
aryloxyalkyl; a C
2
-C
8
alkylthioalkyl; a C
6
-C
10
cycloalkylthioalkyl; a C
7
-C
14
alkylthioaryl; a C
7
-C
14
arylthioalkyl; a C
1
-C
18
alkylamine, disubstituted with C
1
-C
18
linear or branched alkyl; and mi

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